(+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate

Base Information

• Chemical Name: (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate
• CAS No.: 123559-34-2
• Molecular Formula: C₁₆H₃₀O₄Si
• Molecular Weight: 314.497
• Mol file: 123559-34-2.mol

Synonyms:(+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate

Chemical Property of (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate

There total 2 articles about (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

(+/-)-(1S*,3S*)-ethyl-3-hydroxymethyl-5-oxocyclohexylcarboxylate (123559-33-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate (123559-34-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1016/0040-4020(89)80137-1

Reference yield:

(+/-)-(1R*,4S*,6S*,8R*)-1-ethoxy-2-oxatricyclo<4.2.1.04,8>-nonan-7-one dimethylketal (123559-32-0) → (+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate (123559-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / 1percent aq.HCl / ethanol / 15 h / Heating

2: 52 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(89)80137-1

Reference yield: 30.0%

(+/-)-(1S*,3S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-oxocyclohexylcarboxylate (123559-34-2) → (+/-)-(1S*,3S*,5S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-hydroxycyclohexylcarboxylate (123559-35-3,123620-78-0) + (+/-)-(1S*,3S*,5R*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-hydroxycyclohexylcarboxylate (123559-35-3,123620-78-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h;

DOI:10.1016/0040-4020(89)80137-1

upstream raw materials:

(+/-)-(1S*,3S*)-ethyl-3-hydroxymethyl-5-oxocyclohexylcarboxylate

tert-butyldimethylsilyl chloride

(+/-)-(1R*,4S*,6S*,8R*)-1-ethoxy-2-oxatricyclo<4.2.1.0^4,8>-nonan-7-one dimethylketal

Downstream raw materials:

(+/-)-(1S*,3S*,5S*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-hydroxycyclohexylcarboxylate

(+/-)-(1S*,3S*,5R*)-ethyl-3-(tert.-butyldimethylsilyloxy)methyl-5-hydroxycyclohexylcarboxylate